


Jailbreak(s)

by eerian_sadow



Series: PIRATES!! [2]
Category: Transformers - All Media Types, Transformers Generation One
Genre: Alternate Universe, Alternate Universe Pirates, Gen, Implied Prisoner Abuse, Jailbreaks, Mentions of Slavery, Running away from home
Language: English
Status: Completed
Published: 2020-12-31
Updated: 2020-12-31
Packaged: 2021-03-11 02:54:53
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 4,519
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28464168
Author URL: https://archiveofourown.org/users/eerian_sadow/pseuds/eerian_sadow
Summary: Captain Jazz, formerly of the pirate schoonerDawning Hope, has been hired to break a gorgeous woman named Prowl out of the Governor's Mansion and sail away with her. There's just one hold up: she's got to get out of Praxus' prison first.
Relationships: Hound & Bumblebee, Jazz & Bumblebee, Jazz & Hound
Series: PIRATES!! [2]
Series URL: https://archiveofourown.org/series/2084847
Comments: 4
Kudos: 17





	1. Chapter 1

**Author's Note:**

  * For [SunnySidesofBlue](https://archiveofourown.org/users/SunnySidesofBlue/gifts).



> This fic begins a few hours after chapter 1 of "Cages" (found here: https://archiveofourown.org/works/18403145 ) and wraps up before chapter 2 of the same fic. 
> 
> Special thanks to SunnySidesofBlue for supporting this series and this fic in particular. <3

Jazz waited until the guard had done his next patrol through the dungeon before she approached the bars to her cell again. Once he was well out of sight, and likely on his way up to the guardroom upstairs, she pulled the key out of the pouch Prowl had given her and walked quickly to the door. 

There was a scrap of paper wrapped around it, she realized as she reached through the bars, and she told herself to make sure that she took the key when she ran. Whatever note Prowl has written was probably important for this escape.

Her fingers were steady as Jazz inserted the key in the lock and turned. The tumblers gave easily and the door swung open almost immediately after she unlocked it, scraping across the uneven floor of the dungeon. For a heartstopping moment, she froze. When the only sound she heard in response was the coughing of another prisoner, she exhaled softly with relief. 

Then she pulled the key back out of the lock and squeezed through the opening provided by the sloping floor rather than risk pushing it open any further.

The other prisoner coughed again and then a voice rasped, “Take me with you, captain!”

Jazz paused and looked into the other cells until she found the speaker. He was older and weathered, but his eyes were still bright despite the rattling of the breath in his lungs. “Can you sail?”

The older man nodded. “Sail and cook, captain. Please!” 

“All right, long as this key works. I can’t come back for you if it don’t.”

He nodded and backed away from the bars. Jazz put the key in the lock and turned. They both smiled when the lock clicked and the door unlatched. 

“Thank you, captain! I won’t let you down!” The older man pushed the door open and stepped out of the cell. 

“I hope not.” Jazz looked around, trying to find another exit that wouldn’t take them up the stairs and past the guard room. She sighed when she didn’t see an obvious one. “Come on, we’re going up the stairs and out the side door they brought me in through. Stay quiet.”

“Yes, ma’am.” He nodded and coughed again before following her down the hallway. Jazz prayed she wasn't making a huge mistake.

Like the kind of story that one old pirate would tell another in the pub, the guard had actually been sleeping as they sneaked by. Even an ill-timed cough hadn’t ruined their luck, and Jazz had led her fellow prisoner to the safety of the open market fairly quickly. The air was filled with the scents of cooking food, and the purse in her pocket reminded her that she could actually afford more than prison gruel if she wanted to stop for one of the sizzling meat skewers or a sweet bun.

“You hungry?” she asked, gesturing to one of the meat stalls.

“Starving,” he replied. “But I can’t pay. And i’m not looking to get thrown back in prison the same day we got out.”

Jazz shook her head. “I’ve got it. You can pay me back by keeping my crew healthy once we’re back at sea.”

The older man, though he looked younger in the sunlight, nodded. “Thank you, Captain.”

“I’m Jazz, by the way.” She approached the stall selling the skewers, mutton by the smell and accented by a fruit she didn’t recognize, and held up her fingers to indicate she wanted two. “What can I call you?”

“My old crew called me Trailbreaker,” he replied. “I was a navigator, when I wasn’t cooking.”

“Never hurts to have another navigator.” Jazz smiled. She took the skewers when the cook held them out to her and handed him a coin in return. When he tried to protest the amount, she shook her head and turned away, still smiling. She knew she was overpaying, but he would remember her generosity if she came through Praxus again and it also never hurt to have someone owe her a favor. 

“I’d rather cook,” he admitted with a small smile. “But I’ll do whatever needs done, til we have a full crew.”

“Well.” Jazz handed him one of the skewers and then bit into the yellow fruit on hers with a happy sound as she was met with a sweet-tart flavor. “If they haven’t signed onto another ship already, my crew is probably still hiding in town. They took our ship, but I’m the only one who didn’t get away.”

“If they’re looking for work, then they’ll probably be at the Beaded Mermaid. When she’s not serving beer, the owner is sending sailors off to work with decent captains.” Trailbreaker pointed toward the left. “It’s that way, if you want to try it.”

“She got a bath in that pub?” Jazz asked around another mouthful of delightful yellow fruit. She would have to keep an eye out for it in their next port. 

“A bath and there’s a tailor’s shop in the same block.” Trailbreaker coughed again before finally taking a bite of his own food. “A cobbler too, if you need shoes.”

Jazz considered for a moment. Her boots were probably still fine, though after the manure her shirt was a lost cause and her trousers might be, too. “Maybe the next time we come through here. But you need a physician. Or at least an apothecary who knows how to treat that cough.”

“We won’t find either of those in this part of the city.” Trailbreaker shook his head. “And we couldn’t afford them even if we went across the river.”

“Well, we’ll head up the coast a ways and see if we can’t find someone else then. There’s a physician in Vos who don’t mind treating pirates, if that’s where we got to go.”

Trailbreaker smiled. “Thank you, captain. I appreciate that.”


	2. Chapter 2

The Beaded Mermaid was a large pub and inn, denoted by a banner outside featuring a mermaid with skin as dark as Jazz’s and decorated in shining glass beads. The building was in good repair and it was well-lit when they stepped inside. 

It was also busy, packed full of sailors, soldiers and regular citizens alike.

“Trailbreaker!” A woman with the reddest hair Jazz had ever seen stepped out of the crowd and approached them. She dropped two empty cups onto a table as she passed it and then opened her arms toward him with a smile on her face. Trailbreaker stepped forward and hugged her tightly. “When I heard they’d got you, I thought I’d never see you again!”

“I got some help,” Trailbreaker replied. “But I’ll be heading out with her tonight, because the guard will be looking for us.”

“You broke him out for us?” The red haired woman looked over at Jazz. When the captain nodded her smile widened. “We owe you, then. More than we can repay.”

“We need a bath each, Nautica. And clean clothes.” Trailbreaker turned her attention back to him. “And Captain Jazz is looking for her crew.”

“Well, I don’t know that it’s them for sure, but there’s what’s left of a crew in the back room.” Nautica squeezed Trailbreaker again before stepping away. “You know the way to the baths, and I’ll send one of the girls up with clothes for the two of you.”

“Thank you, Nautica.” Trailbreaker smiled and gestured for Jazz to follow. “We’re in your debt.”

“Ain’t no debt here, even if you weren't family. Go get cleaned up before the guard recognizes you.”

The girl who had brought up the clean clothes had the same bright red hair as Nautica and she had stared for several long seconds at Jazz’s back before she remembered to set them down. Jazz had shrugged at the scrutiny, until she asked softly, “Did that hurt?”

Jazz glanced at the scars she could see over her shoulder and shrugged. Then she dunked her head under the water to rinse the soap out of her hair before she answered. “Yeah, it did. Ran away from the man who did it, though. You do the same, if a man comes at you with a cane.”

“I will!” the girl had looked scared, but she hadn’t asked more questions. 

After she was gone, Jazz stepped out of the water and reached for the towel.

She dried and dressed quickly, and once she was satisfied that she looked enough like any other citizen of the city, Jazz made her way back out of the bath house and into the pub. There was still her crew to find, and if she was incredibly lucky, they would be in the back room like Nautica had suggested.

“I asked around, honey,” Nautica appeared by her elbow and pressed a bowl into her hands. The smell of the soup caused her stomach to rumble and remind her that a single stick of grilled meat was not a meal, “And some sailors were real excited to hear your name. I’ve got ‘em waiting in the back room for you. Over there through the yellow curtain.”

“Thank you, miss.” Jazz smiled. “I appreciate the extra work.”

“Ain’t extra. You took care of our Trailbreaker. We’ll take care of you back.” Nautica nudged her with a gentle elbow to the side before she disappeared back into the crowded pub with a swish of skirts. 

Jazz followed her directions and crossed the pub, carefully weaving through the crowd toward the yellow curtain. Once she stepped past it, she was greeted with a welcome sight.

Her crewmates, her family, were almost all in the small room. Hound and Bumblebee looked at her with undisguised delight. Bluestreak bounced on the balls of his feet with happiness. Seaspray and Beachcomber were smiling widely, and Swerve punched the air with a fist.

Jazz smiled so widely it hurt. “Hey, everyone. I guess you missed me?”

She almost spilled her soup when Bumblebee lunged forward to hug her. “How did you get out?”

“I’d like to know that, too,” Hound agreed. “We thought we’d lost you for sure.”

“Well, let me sit down and eat, and I’ll tell you.” Bumblebee didn’t really let go, but he did move enough for her to walk to the table and sit down between him and Hound. “So, I got hired by the prettiest lady I've ever seen while I was in the prison. A hundred gold, a ship, and the key to my cell if I agreed to kidnap her and let her join the crew.”

“You’re kidding!” Hound was disbelieving.

“You made that up so we don’t have to know how bad it was!” Bluestreak agreed.

“I swear to Primus, I did not.” Jazz reached into her pocket and pulled out the purse. She opened it and upended the contents onto the table. Her crew stared at the pile of gold while she picked up the key. “Broke me and another sailor out of the dungeon.”

“Okay, so what’s the catch? It can’t just be that we let her be part of the crew.” Swerve’s earlier excitement faded to doubt. 

“We gotta kidnap her and head back out to sea tonight.”

Silence greeted Jazz’s words. After several long moments, Beachcomber held up his hand and asked, “Tonight-tonight? But we don’t even know where the ship is, if it’s even real.”

Jazz turned the key so that the other pirate could see the paper wrapped around it. “I didn’t have time to read it before, but I hope that’s what this paper tells us.”

“So look already!” Beachcomber was usually incredibly calm, but Jazz didn’t blame him for being worried right now. If he hadn’t talked to Prowl herself, she would be just as worried about being led into a trap.

One pirate was a small sacrifice to possibly capture an entire crew, after all. 

“All right, I’m looking.” Jazz took a quick spoonful of her soup before unrolling the paper. 

_Look for his Lordship’s vessel, the Alpha Trion, at the end of the docks. She should be in slip four, nearest the sea._

“Says the ship we’re looking for is the Alpha Trion, tied up in slip four.”

“That’ll be a lot of open space, Captain.” Bumblebee looked worried now, too. “It’ll be awful easy to get caught.”

“Be easy to get caught no matter what,” Jazz agreed. “But as long as I’m not with you, you look like a regular crew, just getting the ship ready for a morning departure. The governor probably wouldn’t even tell the dockmaster about something like that, if he wanted to leave quickly.”

“The governor? Jazz, who is this woman?” Bee’s worried frown deepened. 

“She’s rich and she’ll be at his party tonight. I didn’t ask for more details. We didn’t have a lot of time.”

“Primus.” Hound dropped his head down against the table. “She’s probably his daughter or something, knowing our luck.”


	3. Chapter 3

Jazz stared at the _Alpha Trion_ with dismay. The handful of her crew that had joined back up with her at the pub was not going to be enough to handle a ship that size. 

“Captain,” Hound said softly, “She’s a lot bigger than our last ship. Should I go back to Nautica’s and hire more hands?”

Jazz considered for a moment before nodding. With the gold Prowl had already paid her, she could compensate a few extra hands to at least help them get to their next port of call. Further, if they managed to raid a merchant or two along the way. “No one who seems too loyal to the governor, though. We’re courting trouble as it is.”

“Aye, Captain. Though you’d court trouble anyway, if she was pretty enough.” Hound winked at her before turning away. “I’ll find people we can trust.”

Jazz grinned. “I know you will. Everyone else, board _quietly_. We want to get her ready to go without drawing too much attention.” 

“You can count on us, Captain!” Bluestreak said seriously. “We’ll be ready as soon as you’re on board.”

“Just be careful, Jazz.” Bumblebee grabbed her hand and squeezed it tightly for a moment. “We can’t come back for you if you get caught again.”

“I know, Bee.” She pulled the small man into a brief hug. “If I’m not back by midnight, take the ship and go. Hound’ll keep you all safe.”

Getting onto the Governor’s property was as easy as Prowl had said it would be. There had been no guards at the gates or in the tower, and the only other person she had seen was an old man with skin nearly as dark as hers, sitting outside a small cabin set away from the main house. Either he hadn’t seen her, or hadn’t cared about her presence, because he hadn’t even looked in her direction as she creeped through the shadows to the enormous garden behind the house.

The garden had been equally unguarded as she made her way through the hedges. Either the governor was so overconfident in his control of the citizens that he didn’t think he needed guards, or he was an idiot. 

When Jazz stepped out of the bushes in front of an impressive fountain, Prowl was perched delicately on a bench with a man who looked a little older than her. Both of them were wearing finery that glittered in the moonlight, but Prowl also seemed to be glowing along with it. Any other night, Jazz would be happy to take the time to appreciate that, too.

Instead, she scraped one boot carefully on the paving stones before ducking back into the bushes. Prowl’s head turned toward the sound, but the man sitting next to her reached out and turned it back toward him. 

“There’s nothing to be concerned about, my dear. Your father hires only the best guards for his estate, you know that.”

Prowl leaned away from him before shaking her head and standing up. “My father’s guards are not my concern this evening. You have forgotten your manners, Lord Powerglide. I am engaged to be married, if you will recall.”

“Engagements can be broken, my dear. You know as well as I that you can do much better than--”

“Indeed, I do.” Prowl turned her back to the noble and glanced carefully at the bushes surrounding the fountain. Jazz put her hand out just far enough that the other woman could see her and Prowl smiled. “Leave me, Lord Powerglide. I have grown weary of your presence.”

Lord Powerglide looked at her with irritation. Then he stood slowly, making a production of stretching before turning toward the house. “As you wish, my dear. May I suggest some refreshments to cool your attitude?”

“You may not.” Prowl’s posture didn’t shift, but Jazz didn’t miss her eyes rolling toward the stars as if asking for patience. “Leave. Me.”

“Your father will hear about this, you realize.”

“Do not presume that you can threaten me. I fear neither my father nor you, in this regard.”

Finally, several long minutes after Prowl stopped talking, Lord Powerglide walked out of the garden. Jazz waited a few more seconds after he was gone before stepping out of the bushes, just to be sure he wasn’t going to turn around and come back.

Prowl’s shoulders relaxed as she looked the pirate over. “I was worried you weren’t coming, when the hour grew so late.”

“Got held up getting the crew onto the ship. You ready to go?”

“Yes, and no. I want to change out of this dress before we leave.” Prowl stepped forward and reached for Jazz’s hand as she walked by. Jazz let her take it and lead her back toward the small cabin she had seen before. “We would never make it past the city guards if I am wearing this much glass.”

Jazz looked at Prowl’s dress more closely as the other woman towed her along. She was right, it was covered in tiny glass beads, and that was what had been sparkling so brightly in the moonlight. “Too bad you can’t bring it. It’d fetch a nice price in Vos.”

“I should hope so, since it was a gift from the Wind Prince himself.” Prowl’s lips quirked up. “He was attempting to secure my father’s favor for a trading agreement regarding the sugar we have begun growing on the island.”

“Where I come from, that would have been a marriage proposal.”

“If our family was slightly more valuable to the King, it would have been. And I would have been much more willing to accept an engagement with the Wind Prince.” Prowl stopped in front of the old man as they reached the cabin. “Is everything ready, Ratchet?”

The old man nodded. “It is. Get changed and make sure you take the rucksack, hear? You’re going to need that fruit out on the water.”

“Yes, Ratchet.” Prowl smiled at him. “Jazz, will you please help me unfasten the buttons? I cannot reach more than the first few on my own.”

“Sure.” They were already running close to the deadline she’d given Bumblebee, but they would be late if she left Prowl to do it on her own. Jazz just hoped the dress didn’t use the kind of loops that they would need a hook to unfasten or she might just cut the buttons off and ruin it, no matter how pretty.


	4. Chapter 4

“I can’t believe we just walked out the front gate!” Jazz laughed as they walked down the street to the ship. “I never would have tried that!”

“Well, it was the front gate or back past Lord Powerglide. Who certainly would have noticed if I had changed dresses.” 

“Yeah, but the guard even wished you a good outing!”

Prowl shrugged. “I often join Lord Mirage in the tavern in the evenings. He likely assumed I was simply meeting my friend, as usual.”

“Alone?” 

“I have you, don’t I, captain? To a tired guard, you look like another handmaid.”

“Glad we both know I’m not that.” Jazz made a face. “I’d rather--”

“HALT!” An unfamiliar voice interrupted them, and both women turned slowly to face the city guard who had stopped them. Jazz did her best not to sigh in defeat.

They had been so, so close.

“State your business.” The guard lifted his lanturn so that he could see them, but he didn’t reach for either the club or the sword on his belt. “What are you doing out so late?”

Prowl lifted her chin, squared her shoulders and glared at the guard. It was the sort of expression Jazz had received from a number of soldiers and guards over the years, but it was twice as intimidating coming from Prowl, with her sharp blue eyes. “We are on an urgent errand for my father. How dare you delay us?”

Unlike Jazz, the guard didn’t seem intimidated by Prowl’s glare at all. He glanced at their rucksacks--Ratchet hadn’t hesitated to shove more fruit into Jazz’s hands as they left--and smirked. “I suppose your urgent errand is to deliver a lost order?”

“Miss, we’ll delay the ship,” Jazz stage whispered, taking on the part of nervous handmaid, even though she didn’t like the idea. “The captain said we can’t miss the tide!”

“Unfortunately, my handmaid is correct.” Prowl started to turn away. “We must board our ship and be on our way to Iacon before the tide goes out. My father, the governor, would be most upset if he finds out that we were delayed until morning because of your questioning.”

At the mention of the governor, the guard blanched. “I beg your pardon, Miss. I didn’t recognize you.”

“You are forgiven, so long as we may pass without further incident.” Prowl was already walking away and Jazz hurried to follow. 

“Of course, Miss. Have a good night, Miss!”

“Be quick,” Prowl whispered. “He’ll come to his senses quickly once he realizes that he hasn’t seen anyone with luggage coming through this part of the city.”

“At least what I said about the tide is true,” Jazz gave her a rueful smile. “We will be stuck in the harbor til morning if it’s much longer before we board. We’d hang up on the reef and the navy would be on us before we could dive overboard.”

“Hey, wait!” The guard shouted and Jazz heard someone running toward them.

“Prowl, run!” Jazz took off in a sprint, hoping the other woman could keep up. She really, really didn’t want to leave Prowl behind, but if the whole guard was called out, she would do what she had to to keep herself from going back to prison and the gallows. 

“Follow me.” Prowl was not only keeping up, she was a little faster, and she grabbed Jazz by the wrist to drag her along in the right direction. They ran toward the bright lights of a tavern--one that was made from much more expensive materials than Nautica’s--and a small knot of well dressed young men. “When we get to the tavern, play along!”

“You got it!” Despite their situation, Jazz smiled. Prowl was starting to look like she might already have the makings of a pirate.

“Please, you have to help us!” Prowl grabbed the arm of one of the men and tugged insistently. “Please! We’re being chased by a man who tried to… to…”

Jazz crossed her arms over her chest like she’d been groped and was upset about it. “He touched us, sir.”

The young man looked both drunk and angry, and Jazz thought that was going to help them a great deal tonight. “That fiend! I will teach him a lesson he won’t soon forget! Where can I find him?”

“Following us! The man in the guard’s uniform!” Prowl pointed as the guard rounded a corner and continued running toward them.

“Fear not, m’lady! I will teach him manners!” The young man stepped forward to put himself between Prowl and the guard, an action his friends copied a moment later. 

“Get out of the way! You’re interfering in guard business!” The young men grabbed the guard before he could say anything else. Jazz and Prowl watched just long enough to see that they restrained him thoroughly, then they turned and ran toward the docks again. 

“Once we’re far from Praxus, remind me to send that young man a thank you letter.” Prowl smiled briefly. “If we’re fortunate, he will even remember why he ended up in the prison tonight.”

“I’ll send one myself,” Jazz agreed, “As long as we make it onto the ship.”


	5. Chapter 5

“Bumblebee, you heard the captain’s orders as well as I did.” Hound put a comforting hand on the smaller man’s shoulder. “It’s past midnight. We have to go.”

Bumblebee shook his head. “Not yet. I know she’s coming.”

“Bee…” Hound’s voice held a tone that was almost pity.

“She’s coming. Jazz wouldn’t leave us like this.”

“Fine. We’ll give her a few more minutes. But no more than that or we’ll miss the tide.”

Bumblebee frowned, but he nodded. “Thanks, Hound.”

“I just hope this doesn’t get us all caught.”

“We’ll be all right.” Bee turned and stared out into the city, looking for any sign of their captain.

A moment later, he heard the echo of running footsteps. Then he saw the captain and another woman step into the light, running as fast as they could. Another moment later, laughter echoed along the dock.

“Looks like you were right after all, Bee.” Hound patted his shoulder again and turned to the rest of the crew. “Loosen the moorings! Weigh anchor! We depart the moment the captain is on board!”

A chorus of “Aye, sir!” replied to the orders and Bee crouched down and took hold of the gangplank. He’d pull it up behind the captain and their guest… crewmate, if she really decided to stay. And then he would punch her in the shoulder for making them all worry.

“I told you not to wait, Hound!” Jazz’s voice came up the plank before she did, and Bumblebee was glad to hear it. She didn’t sound too angry with them. “But I’m glad you did. Ain’t nothin’ else in this port small enough to steal and meet up with you in.”

“Thank Bumblebee, Captain.” Hound didn’t hesitate to pull Jazz into a brief hug as she stepped onto the deck. “He wouldn’t leave without you.”

“Just for that, you can get these put away in the mess.” Jazz set a bag down in front of him before turning to help their new crewmate onto the ship. “Prowl, these are my crewmates Hound and Bumblebee. They’re my most trusted friends. Hound, Bee, our employer, Prowl.”

“One of you soon, I hope.” The blond woman smiled and dropped her own bag next to Jazz’s. 

“Once we’re out in the open sea,” Jazz agreed. “They won’t take you back without one hell of a fight.”

Bumblebee didn’t miss the way Prowl’s shoulders relaxed at the captain’s words. Silently, he vowed to himself that whoever she was running away from would never take her back alive.


End file.
